U.S. patent application number 13/931829 was filed with the patent office on 2013-11-14 for compound for organic optoelectronic device, organic light emitting diode including the same and display including the organic light emitting diode.
The applicant listed for this patent is Mi-Young CHAE, Ho-Kuk JUNG, Dong-Min KANG, Eui-Su KANG, Myeong-Soon KANG, Nam-Soo KIM, Nam-Heon LEE. Invention is credited to Mi-Young CHAE, Ho-Kuk JUNG, Dong-Min KANG, Eui-Su KANG, Myeong-Soon KANG, Nam-Soo KIM, Nam-Heon LEE.
Application Number | 20130299794 13/931829 |
Document ID | / |
Family ID | 46383296 |
Filed Date | 2013-11-14 |
United States Patent
Application |
20130299794 |
Kind Code |
A1 |
JUNG; Ho-Kuk ; et
al. |
November 14, 2013 |
COMPOUND FOR ORGANIC OPTOELECTRONIC DEVICE, ORGANIC LIGHT EMITTING
DIODE INCLUDING THE SAME AND DISPLAY INCLUDING THE ORGANIC LIGHT
EMITTING DIODE
Abstract
A compound for an organic optoelectronic device, the compound
being represented by the following Chemical Formula 1:
##STR00001##
Inventors: |
JUNG; Ho-Kuk; (Uiwang-si,
KR) ; KANG; Dong-Min; (Uiwang-si, KR) ; KANG;
Myeong-Soon; (Uiwang-si, KR) ; KANG; Eui-Su;
(Uiwang-si, KR) ; KIM; Nam-Soo; (Uiwang-si,
KR) ; LEE; Nam-Heon; (Uiwang-si, KR) ; CHAE;
Mi-Young; (Uiwang-si, KR) |
|
Applicant: |
Name |
City |
State |
Country |
Type |
JUNG; Ho-Kuk
KANG; Dong-Min
KANG; Myeong-Soon
KANG; Eui-Su
KIM; Nam-Soo
LEE; Nam-Heon
CHAE; Mi-Young |
Uiwang-si
Uiwang-si
Uiwang-si
Uiwang-si
Uiwang-si
Uiwang-si
Uiwang-si |
|
KR
KR
KR
KR
KR
KR
KR |
|
|
Family ID: |
46383296 |
Appl. No.: |
13/931829 |
Filed: |
June 29, 2013 |
Related U.S. Patent Documents
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Application
Number |
Filing Date |
Patent Number |
|
|
PCT/KR2011/005378 |
Jul 21, 2011 |
|
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|
13931829 |
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Current U.S.
Class: |
257/40 ;
544/333 |
Current CPC
Class: |
C09K 2211/1011 20130101;
C09K 2211/1044 20130101; H01L 51/5056 20130101; H01L 51/0072
20130101; H05B 33/10 20130101; H01L 51/0067 20130101; C09B 57/00
20130101; H01L 51/5072 20130101; C09K 11/06 20130101; C09K
2211/1007 20130101; C09K 2211/1029 20130101; C09K 2211/1059
20130101; Y02E 10/549 20130101; H01L 51/0058 20130101 |
Class at
Publication: |
257/40 ;
544/333 |
International
Class: |
H01L 51/00 20060101
H01L051/00 |
Foreign Application Data
Date |
Code |
Application Number |
Dec 31, 2010 |
KR |
10-2010-0140595 |
Claims
1. A compound for an organic optoelectronic device, the compound
being represented by the following Chemical Formula 1: ##STR00104##
wherein, in Chemical Formula 1, X.sup.1 to X.sup.4 are each
independently --N--, --CR.sup.1--, --CR.sup.2--, --CR.sup.3-- or
--CR.sup.4--, R.sup.1 to R.sup.4 are each independently hydrogen,
deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a
substituted or unsubstituted C6 to C30 aryl group, a substituted or
unsubstituted C3 to C30 heteroaryl group, or a combination thereof,
L.sup.1 and L.sup.2 are each independently a single bond, a
substituted or unsubstituted C2 to C6 alkenyl group, a substituted
or unsubstituted C2 to C6 alkynyl group, a substituted or
unsubstituted C6 to C30 arylene group, a substituted or
unsubstituted C3 to C30 heteroarylene group, or a combination
thereof, n and m are each independently 1 or 2, Ar.sup.1 and
Ar.sup.2 are each independently hydrogen, deuterium, a substituted
or unsubstituted C1 to C20 alkyl group, a substituted or
unsubstituted C6 to C30 aryl group, a substituted or unsubstituted
C3 to C30 heteroaryl group, or a combination thereof, and at least
one of Ar.sup.1 or Ar.sup.2 is a substituted or unsubstituted C3 to
C30 heteroaryl group having electronic properties.
2. The compound for an organic optoelectronic device as claimed in
claim 1, wherein the compound is represented by the following
Chemical Formula 2: ##STR00105## wherein, in Chemical Formula 2,
X.sup.1 to X.sup.4 are each independently --N--, --CR.sup.1--,
--CR.sup.2--, --CR.sup.3-- or --CR.sup.4--, R.sup.1 to R.sup.6 are
each independently hydrogen, deuterium, a substituted or
unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted
C6 to C30 aryl group, a substituted or unsubstituted C3 to C30
heteroaryl group, or a combination thereof, L.sup.1 and L.sup.2 are
each independently a single bond, a substituted or unsubstituted C2
to C6 alkenyl group, a substituted or unsubstituted C2 to C6
alkynyl group, a substituted or unsubstituted C6 to C30 arylene
group, a substituted or unsubstituted C3 to C30 heteroarylene
group, or a combination thereof, n and m are each independently 1
or 2, Ar.sup.2 is hydrogen, deuterium, a substituted or
unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted
C6 to C30 aryl group, a substituted or unsubstituted C3 to C30
heteroaryl group, or a combination thereof, X.sup.5 to X.sup.7 are
each independently --N-- or --CR'--, wherein R' is hydrogen or
deuterium, and at least one of X.sup.5 to X.sup.7 is --N--.
3. The compound for an organic optoelectronic device as claimed in
claim 2, wherein Ar.sup.2 is a substituted or unsubstituted
naphthyl group, a substituted or unsubstituted anthracenyl group, a
substituted or unsubstituted phenanthrenyl group, a substituted or
unsubstituted triphenylenyl group, a substituted or unsubstituted
pyrenyl group, a substituted or unsubstituted chrysenyl group, or a
combination thereof.
4. The compound for an organic optoelectronic device as claimed in
claim 1, wherein the compound is represented by the following
Chemical Formula 3: ##STR00106## wherein, in Chemical Formula 3,
X.sup.1 to X.sup.4 are each independently --N--, --CR.sup.1--,
--CR.sup.2--, --CR.sup.3-- or --CR.sup.4--, R.sup.1 to R.sup.6 are
each independently hydrogen, deuterium, a substituted or
unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted
C6 to C30 aryl group, a substituted or unsubstituted C3 to C30
heteroaryl group, or a combination thereof, L.sup.1 and L.sup.2 are
each independently a single bond, a substituted or unsubstituted C2
to C6 alkenyl group, a substituted or unsubstituted C2 to C6
alkynyl group, a substituted or unsubstituted C6 to C30 arylene
group, a substituted or unsubstituted C3 to C30 heteroarylene
group, or a combination thereof, n and m are each independently 1
or 2, Ar.sup.1 is hydrogen, deuterium, a substituted or
unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted
C6 to C30 aryl group, a substituted or unsubstituted C3 to C30
heteroaryl group, or a combination thereof, X.sup.5 to X.sup.7 are
each independently --N-- or --CR'--, wherein R' is hydrogen or
deuterium, and at least one of X.sup.5 to X.sup.7 is --N--.
5. The compound for an organic optoelectronic device as claimed in
claim 3, wherein Ar.sup.1 is a substituted or unsubstituted
naphthyl group, a substituted or unsubstituted anthracenyl group, a
substituted or unsubstituted phenanthrenyl group, a substituted or
unsubstituted triphenylenyl group, a substituted or unsubstituted
pyrenyl group, a substituted or unsubstituted chrysenyl group, or a
combination thereof.
6. The compound for an organic optoelectronic device as claimed in
claim 1, wherein the substituted or unsubstituted C3 to C30
heteroaryl group having the electronic properties is a substituted
or unsubstituted imidazolyl group, a substituted or unsubstituted
triazolyl group, a substituted or unsubstituted tetrazolyl group, a
substituted or unsubstituted carbazolyl group, a substituted or
unsubstituted oxadiazolyl group, a substituted or unsubstituted
oxatriazolyl group, a substituted or unsubstituted thiatriazolyl
group, a substituted or unsubstituted benzimidazolyl group, a
substituted or unsubstituted benzotriazolyl group, a substituted or
unsubstituted pyridinyl group, a substituted or unsubstituted
pyrimidinyl group, a substituted or unsubstituted triazinyl group,
a substituted or unsubstituted pyrazinyl group, a substituted or
unsubstituted pyridazinyl group, a substituted or unsubstituted
purinyl group, a substituted or unsubstituted quinolinyl group, a
substituted or unsubstituted isoquinolinyl group, a substituted or
unsubstituted phthalazinyl group, a substituted or unsubstituted
naphpyridinyl group, a substituted or unsubstituted quinoxalinyl
group, a substituted or unsubstituted quinazolinyl group, a
substituted or unsubstituted acridinyl group, a substituted or
unsubstituted phenanthrolinyl group, a substituted or unsubstituted
phenazinyl group, or a combination thereof.
7. The compound for an organic optoelectronic device as claimed in
claim 1, wherein the compound is represented by one of the
following Chemical Formulae A1 to A63: ##STR00107## ##STR00108##
##STR00109## ##STR00110## ##STR00111## ##STR00112## ##STR00113##
##STR00114## ##STR00115## ##STR00116## ##STR00117## ##STR00118##
##STR00119## ##STR00120## ##STR00121## ##STR00122## ##STR00123##
##STR00124## ##STR00125## ##STR00126## ##STR00127##
8. The compound for an organic optoelectronic device as claimed in
claim 1, wherein the compound is represented by one of the
following Chemical Formulae B1 to B72: ##STR00128## ##STR00129##
##STR00130## ##STR00131## ##STR00132## ##STR00133## ##STR00134##
##STR00135## ##STR00136## ##STR00137## ##STR00138## ##STR00139##
##STR00140## ##STR00141## ##STR00142## ##STR00143## ##STR00144##
##STR00145## ##STR00146## ##STR00147## ##STR00148## ##STR00149##
##STR00150## ##STR00151##
9. The compound for an organic optoelectronic device as claimed in
claim 1, wherein the organic optoelectronic device is selected from
the group of an organic light emitting diode, an organic solar
cell, an organic transistor, an organic photo-conductor drum, and
an organic memory device.
10. An organic light emitting diode, comprising: an anode; a
cathode; and at least one organic thin layer between the anode and
cathode, wherein the at least one organic thin layer includes the
compound for an organic optoelectronic device as claimed in claim
1.
11. The organic light emitting diode as claimed in claim 10,
wherein the at least one organic thin layer includes one selected
from the group of an emission layer, a hole transport layer (HTL),
a hole injection layer (HIL), an electron transport layer (ETL), an
electron injection layer (EIL), a hole blocking layer, and a
combination thereof.
12. The organic light emitting diode as claimed in claim 10,
wherein: the at least one organic thin layer includes an electron
transport layer (ETL) or an electron injection layer (EIL), and the
compound for an organic optoelectronic device is included in the
electron transport layer (ETL) or the electron injection layer
(EIL).
13. The organic light emitting diode as claimed in claim 10,
wherein: the at least one organic thin layer includes an emission
layer, and the compound for an organic optoelectronic device is
included in the emission layer.
14. The organic light emitting diode as claimed in claim 10,
wherein: the at least one organic thin layer includes an emission
layer, and the compound for an organic optoelectronic device is a
phosphorescent or fluorescent host material in the emission
layer.
15. The organic light emitting diode as claimed in claim 10,
wherein: the at least one organic thin layer includes an emission
layer, and the compound for an organic optoelectronic device is a
fluorescent blue dopant material in the emission layer.
16. A display device comprising the organic light emitting diode as
claimed in claim 10.
Description
CROSS-REFERENCE TO RELATED APPLICATIONS
[0001] This application is a continuation of pending International
Application No. PCT/KR2011/005378, entitled "Compound for Organic
Optoelectronic Device, Organic Light Emitting Diode Including the
Same and Display Including the Organic Light Emitting Diode," which
was filed on Jul. 21, 2011, the entire contents of which are hereby
incorporated by reference.
[0002] Korean Patent Application No. 10-2010-0140595, filed on Dec.
31, 2010, in the Korean Intellectual Property Office, and entitled:
"Compound for Organic Optoelectronic Device, Organic Light Emitting
Diode Including the Same and Display Including the Organic Light
Emitting Diode," is incorporated by reference herein in its
entirety.
BACKGROUND
[0003] 1. Field
[0004] Embodiments relate to a compound for an organic
optoelectronic device, an organic light emitting diode including
the same, and a display device including the organic light emitting
diode.
[0005] 2. Description of the Related Art
[0006] An organic optoelectronic device is, in a broad sense, a
device for transforming photo-energy to electrical energy or
conversely, a device for transforming electrical energy to
photo-energy.
[0007] An organic optoelectronic device may be classified as
follows in accordance with its driving principles. One type of
organic optoelectronic device is an electronic device driven as
follows: excitons are generated in an organic material layer by
photons from an external light source; the excitons are separated
into electrons and holes; and the electrons and holes are
transferred to different electrodes as a current source (voltage
source).
[0008] Another type of organic optoelectronic device is an
electronic device driven as follows: a voltage or a current is
applied to at least two electrodes to inject holes and/or electrons
into an organic material semiconductor positioned at an interface
of the electrodes, and the device is driven by the injected
electrons and holes.
[0009] Examples of the organic optoelectronic device may include an
organic light emitting diode, an organic solar cell, an organic
photo conductor drum, and an organic transistor, and the like,
which require a hole injecting or transport material, an electron
injecting or transport material, or a light emitting material.
SUMMARY
[0010] Embodiments are directed to a compound for an organic
optoelectronic device, an organic light emitting diode including
the same, and a display device including the organic light emitting
diode.
[0011] The embodiments may be realized by providing a compound for
an organic optoelectronic device, the compound being represented by
the following Chemical Formula 1:
##STR00002##
[0012] wherein, in Chemical Formula 1, X.sup.1 to X.sup.4 are each
independently --N--, --CR.sup.1--, --CR.sup.2--, --CR.sup.3-- or
--CR.sup.4--, R.sup.1 to R.sup.4 are each independently hydrogen,
deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a
substituted or unsubstituted C6 to C30 aryl group, a substituted or
unsubstituted C3 to C30 heteroaryl group, or a combination thereof,
L.sup.1 and L.sup.2 are each independently a single bond, a
substituted or unsubstituted C2 to C6 alkenyl group, a substituted
or unsubstituted C2 to C6 alkynyl group, a substituted or
unsubstituted C6 to C30 arylene group, a substituted or
unsubstituted C3 to C30 heteroarylene group, or a combination
thereof, n and m are each independently 1 or 2, Ar.sup.1 and
Ar.sup.2 are each independently hydrogen, deuterium, a substituted
or unsubstituted C1 to C20 alkyl group, a substituted or
unsubstituted C6 to C30 aryl group, a substituted or unsubstituted
C3 to C30 heteroaryl group, or a combination thereof, and at least
one of Ar.sup.1 or Ar.sup.2 is a substituted or unsubstituted C3 to
C30 heteroaryl group having electronic properties.
[0013] The compound may be represented by the following Chemical
Formula 2:
##STR00003##
[0014] wherein, in Chemical Formula 2, X.sup.1 to X.sup.4 are each
independently --N--, --CR.sup.1--, --CR.sup.2--, --CR.sup.3-- or
--CR.sup.4--, R.sup.1 to R.sup.6 are each independently hydrogen,
deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a
substituted or unsubstituted C6 to C30 aryl group, a substituted or
unsubstituted C3 to C30 heteroaryl group, or a combination thereof,
L.sup.1 and L.sup.2 are each independently a single bond, a
substituted or unsubstituted C2 to C6 alkenyl group, a substituted
or unsubstituted C2 to C6 alkynyl group, a substituted or
unsubstituted C6 to C30 arylene group, a substituted or
unsubstituted C3 to C30 heteroarylene group, or a combination
thereof, n and m are each independently 1 or 2, Ar.sup.2 is
hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl
group, a substituted or unsubstituted C6 to C30 aryl group, a
substituted or unsubstituted C3 to C30 heteroaryl group, or a
combination thereof, X.sup.5 to X.sup.7 are each independently
--N-- or --CR'--, wherein R' is hydrogen or deuterium, and at least
one of X.sup.5 to X.sup.7 is --N--.
[0015] Ar.sup.2 may be a substituted or unsubstituted naphthyl
group, a substituted or unsubstituted anthracenyl group, a
substituted or unsubstituted phenanthrenyl group, a substituted or
unsubstituted triphenylenyl group, a substituted or unsubstituted
pyrenyl group, a substituted or unsubstituted chrysenyl group, or a
combination thereof.
[0016] The compound may be represented by the following Chemical
Formula 3:
##STR00004##
[0017] wherein, in Chemical Formula 3, X.sup.1 to X.sup.4 are each
independently --N--, --CR.sup.1--, --CR.sup.2--, --CR.sup.3-- or
--CR.sup.4--, R.sup.1 to R.sup.6 are each independently hydrogen,
deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a
substituted or unsubstituted C6 to C30 aryl group, a substituted or
unsubstituted C3 to C30 heteroaryl group, or a combination thereof,
L.sup.1 and L.sup.2 are each independently a single bond, a
substituted or unsubstituted C2 to C6 alkenyl group, a substituted
or unsubstituted C2 to C6 alkynyl group, a substituted or
unsubstituted C6 to C30 arylene group, a substituted or
unsubstituted C3 to C30 heteroarylene group, or a combination
thereof, n and m are each independently 1 or 2, Ar.sup.1 is
hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl
group, a substituted or unsubstituted C6 to C30 aryl group, a
substituted or unsubstituted C3 to C30 heteroaryl group, or a
combination thereof, X.sup.5 to X.sup.7 are each independently
--N-- or --CR'--, wherein R' is hydrogen or deuterium, and at least
one of X.sup.5 to X.sup.7 is --N--.
[0018] Ar.sup.1 may be a substituted or unsubstituted naphthyl
group, a substituted or unsubstituted anthracenyl group, a
substituted or unsubstituted phenanthrenyl group, a substituted or
unsubstituted triphenylenyl group, a substituted or unsubstituted
pyrenyl group, a substituted or unsubstituted chrysenyl group, or a
combination thereof.
[0019] The substituted or unsubstituted C3 to C30 heteroaryl group
having the electronic properties may be a substituted or
unsubstituted imidazolyl group, a substituted or unsubstituted
triazolyl group, a substituted or unsubstituted tetrazolyl group, a
substituted or unsubstituted carbazolyl group, a substituted or
unsubstituted oxadiazolyl group, a substituted or unsubstituted
oxatriazolyl group, a substituted or unsubstituted thiatriazolyl
group, a substituted or unsubstituted benzimidazolyl group, a
substituted or unsubstituted benzotriazolyl group, a substituted or
unsubstituted pyridinyl group, a substituted or unsubstituted
pyrimidinyl group, a substituted or unsubstituted triazinyl group,
a substituted or unsubstituted pyrazinyl group, a substituted or
unsubstituted pyridazinyl group, a substituted or unsubstituted
purinyl group, a substituted or unsubstituted quinolinyl group, a
substituted or unsubstituted isoquinolinyl group, a substituted or
unsubstituted phthalazinyl group, a substituted or unsubstituted
naphpyridinyl group, a substituted or unsubstituted quinoxalinyl
group, a substituted or unsubstituted quinazolinyl group, a
substituted or unsubstituted acridinyl group, a substituted or
unsubstituted phenanthrolinyl group, a substituted or unsubstituted
phenazinyl group, or a combination thereof.
[0020] The compound may be represented by one of the following
Chemical Formulae A1 to A63:
##STR00005## ##STR00006## ##STR00007## ##STR00008## ##STR00009##
##STR00010## ##STR00011## ##STR00012## ##STR00013## ##STR00014##
##STR00015## ##STR00016## ##STR00017## ##STR00018## ##STR00019##
##STR00020## ##STR00021## ##STR00022## ##STR00023## ##STR00024##
##STR00025##
[0021] The compound may be represented by one of the following
Chemical Formulae B1 to B72:
##STR00026## ##STR00027## ##STR00028## ##STR00029## ##STR00030##
##STR00031## ##STR00032## ##STR00033## ##STR00034## ##STR00035##
##STR00036## ##STR00037## ##STR00038## ##STR00039## ##STR00040##
##STR00041## ##STR00042## ##STR00043## ##STR00044## ##STR00045##
##STR00046## ##STR00047## ##STR00048## ##STR00049##
[0022] The organic optoelectronic device may be selected from the
group of an organic light emitting diode, an organic solar cell, an
organic transistor, an organic photo-conductor drum, and an organic
memory device.
[0023] The embodiments may also be realized by providing an organic
light emitting diode including an anode; a cathode; and at least
one organic thin layer between the anode and cathode, wherein the
at least one organic thin layer includes the compound for an
organic optoelectronic device according to an embodiment.
[0024] The the at least one organic thin layer may include one
selected from the group of an emission layer, a hole transport
layer (HTL), a hole injection layer (HIL), an electron transport
layer (ETL), an electron injection layer (EIL), a hole blocking
layer, and a combination thereof.
[0025] The at least one organic thin layer may include an electron
transport layer (ETL) or an electron injection layer (EIL), and the
compound for an organic optoelectronic device may be included in
the electron transport layer (ETL) or the electron injection layer
(EIL).
[0026] The at least one organic thin layer may include an emission
layer, and the compound for an organic optoelectronic device may be
included in the emission layer.
[0027] The at least one organic thin layer may include an emission
layer, and the compound for an organic optoelectronic device may be
a phosphorescent or fluorescent host material in the emission
layer.
[0028] The at least one organic thin layer may include an emission
layer, and the compound for an organic optoelectronic device may be
a fluorescent blue dopant material in the emission layer.
[0029] The embodiments may also be realized by providing a display
device comprising the organic light emitting diode according to an
embodiment.
BRIEF DESCRIPTION OF THE DRAWINGS
[0030] Features will become apparent to those of skill in the art
by describing in detail exemplary embodiments with reference to the
attached drawings in which:
[0031] FIGS. 1 to 5 illustrate cross-sectional views showing
organic light emitting diodes according to various embodiments.
[0032] FIG. 6 illustrates a graph showing changes in current
density depending on a voltage of devices according to Examples 3
and 4 and Comparative Example 1.
[0033] FIG. 7 illustrates a graph showing changes in current
density depending on a voltage of devices according to Examples 5
and 6 and Comparative Example 2.
[0034] FIG. 8 illustrates a graph showing changes in luminance
depending on a voltage of devices according to Examples 3 and 4 and
Comparative Example 1.
[0035] FIG. 9 illustrates a graph showing changes in luminance
depending on a voltage of devices according to Examples 5 and 6 and
Comparative Example 2.
[0036] FIG. 10 illustrates a graph showing changes in luminous
efficiency depending on luminance of devices according to Examples
3 and 4 and Comparative Example 1.
[0037] FIG. 11 illustrates a graph showing changes in luminous
efficiency depending on luminance of devices according to Examples
5 and 6 and Comparative Example 2.
[0038] FIG. 12 illustrates a graph showing changes in electric
power efficiency depending on luminance of devices according to
Examples 3 and 4 and Comparative Example 1.
[0039] FIG. 13 illustrates a graph showing changes in electric
power efficiency depending on luminance of devices according to
Examples 5 and 6 and Comparative Example 2.
DETAILED DESCRIPTION
[0040] Example embodiments will now be described more fully
hereinafter with reference to the accompanying drawings; however,
they may be embodied in different forms and should not be construed
as limited to the embodiments set forth herein. Rather, these
embodiments are provided so that this disclosure will be thorough
and complete, and will fully convey exemplary implementations to
those skilled in the art.
[0041] In the drawing figures, the dimensions of layers and regions
may be exaggerated for clarity of illustration. Like reference
numerals refer to like elements throughout.
[0042] As used herein, when specific definition is not otherwise
provided, the term "substituted" may refer to one substituted with
a C1 to C30 alkyl group, a C1 to C10 alkylsilyl group, a C3 to C30
cycloalkyl group, a C6 to C30 aryl group, a C1 to C10 alkoxy group,
a fluoro group, C1 to C10 trifluoroalkyl group such as a
trifluoromethyl group, and the like, or a cyano group.
[0043] As used herein, when specific definition is not otherwise
provided, the term "hetero" may refer to one including 1 to 3
hetero atoms selected from the group of N, O, S, and P, and
remaining carbons in one functional group.
[0044] As used herein, when a definition is not otherwise provided,
the term "combination thereof" may refer to at least two
substituents bound to each other by a linker, or at least two
substituents condensed to each other.
[0045] In the specification, when a definition is not otherwise
provided, the term "alkyl group" may refer to an aliphatic
hydrocarbon group. The alkyl group may be to a saturated group
without any alkene group or alkyne group.
[0046] The alkyl group may be branched, linear, or cyclic
regardless of being saturated or unsaturated.
[0047] The alkyl group may be a C1 to C20 alkyl group. The alkyl
group may be a C1 to C10 medium-sized alkyl group. The alkyl group
may be a C1 to C6 lower alkyl group.
[0048] For example, a C1 to C4 alkyl group may have 1 to 4 carbon
atoms and may be selected from the group consisting of methyl,
ethyl, propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, and
t-butyl.
[0049] Typical examples of an alkyl group may be individually and
independently selected from a methyl group, an ethyl group, a
propyl group, an isopropyl group, a butyl group, an isobutyl group,
a t-butyl group, a pentyl group, a hexyl group, a cyclopropyl
group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group,
and the like or a functional group substituted with one or more
foregoing groups.
[0050] The "alkene group" may refer to a substituent of at least
one carbon-carbon double bond of at least two carbons, and the
"alkyne group" may refer to a substituent of at least one
carbon-carbon triple bond of at least two carbons.
[0051] The "aromatic group" may refer to a substituent including
all element of the cycle having p-orbitals which form conjugation.
Examples may include an aryl group and a heteroaryl group.
[0052] The "aryl group" may refer to a monocyclic or fused ring
polycyclic (i.e., rings sharing adjacent pairs of carbon atoms)
substituent.
[0053] The "heteroaryl group" may refer to an aryl group including
1 to 3 hetero atoms selected from the group consisting of N, O, S,
and P, and remaining carbons in one functional group.
[0054] "Spiro structure" may refer to a plurality of cyclic
structures having a contact point of one carbon. The Spiro
structure may include a compound having a spiro structure or a
substituent having a spiro structure.
[0055] An embodiment provides a compound for an organic
optoelectronic device represented by the following Chemical Formula
1.
##STR00050##
[0056] In Chemical Formula 1, X.sup.1 to X.sup.4 may each
independently be --N--, --CR.sup.1--, --CR.sup.2--, --CR.sup.3-- or
--CR.sup.4--, R.sup.1 to R.sup.4 may each independently be a
hydrogen, deuterium, substituted or unsubstituted C1 to C20 alkyl
group, substituted or unsubstituted C6 to C30 aryl group,
substituted or unsubstituted C3 to C30 heteroaryl group, or a
combination thereof, L.sup.1 and L.sup.2 may each independently be
a single bond, substituted or unsubstituted C2 to C6 alkenyl group,
substituted or unsubstituted C2 to C6 alkynyl group, substituted or
unsubstituted C6 to C30 arylene group, substituted or unsubstituted
C3 to C30 heteroarylene group, or a combination thereof, n and m
may each independently be 1 or 2, Ar.sup.1 and Ar.sup.2 may each
independently be hydrogen, deuterium, a substituted or
unsubstituted C1 to C20 alkyl group, substituted or unsubstituted
C6 to C30 aryl group, a substituted or unsubstituted C3 to C30
heteroaryl group, or a combination thereof.
[0057] In an implementation, at least one of Ar.sup.1 or Ar.sup.2
may be a substituted or unsubstituted C3 to C30 heteroaryl group
having electronic properties. The electronic properties may refer
to electron injection and/or transport properties.
[0058] The compound for an organic optoelectronic device
represented by the above Chemical Formula 1 may have a structure
including a substituent having electronic properties on a fused
ring core including at least two nitrogen atoms.
[0059] Characteristics of the entire compound may be controlled by
introducing an appropriate substituent (onto the core structure)
having excellent electronic properties.
[0060] The compound for an organic optoelectronic device may
include a core part and various substituents for substituting the
core part. Thus, the compound may have various energy band gaps.
The compound may be used in an electron injection layer (EIL) and
an electron transport layer (ETL), or an emission layer.
[0061] The compound may have an appropriate energy level, depending
on the substituents. Thus, the compound may fortify electron
transport capability of an organic photoelectric device and may
bring about excellent effects on efficiency and driving voltage and
also, may have excellent electrochemical and thermal stability.
Thus, life-span characteristic during the operation of the organic
photoelectric device may be improved.
[0062] As noted above, the electronic properties may refer to a
characteristic in which an electron formed in the cathode is easily
injected into the emission layer and transported in the emission
layer due to conductive properties according to LUMO level. For
example, the electronic properties may refer to an electron
injection or transport properties.
[0063] Hole properties may refer to characteristics in which a hole
formed in the anode is easily injected into the emission layer and
transported in the emission layer due to conductive characteristic
according to HOMO level.
[0064] The structure of the compound may have an asymmetric bipolar
characteristic by appropriately blending or selecting a
substituent. For example, the structure of asymmetric bipolar
characteristic may help improve electron transport properties, so
it may be expected that the luminous efficiency and the performance
of the device using the same may be improved.
[0065] Examples of the compound represented by the above Chemical
Formula 1 may be represented by one of the following Chemical
Formula 2 or 3.
##STR00051##
[0066] In Chemical Formula 2, X.sup.1 to X.sup.4 may each
independently be --N--, --CR.sup.1--, --CR.sup.2--, --CR.sup.3-- or
--CR.sup.4--, R.sup.1 to R.sup.6 may each independently be a
hydrogen, deuterium, substituted or unsubstituted C1 to C20 alkyl
group, substituted or unsubstituted C6 to C30 aryl group,
substituted or unsubstituted C3 to C30 heteroaryl group, or a
combination thereof, L.sup.1 and L.sup.2 may each independently be
a single bond, substituted or unsubstituted C2 to C6 alkenyl group,
substituted or unsubstituted C2 to C6 alkynyl group, substituted or
unsubstituted C6 to C30 arylene group, substituted or unsubstituted
C3 to C30 heteroarylene group, or a combination thereof, n and m
may each independently be 1 or 2, Ar.sup.2 may be hydrogen,
deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a
substituted or unsubstituted C6 to C30 aryl group, a substituted or
unsubstituted C3 to C30 heteroaryl group, or a combination thereof,
X.sup.5 to X.sup.7 may each independently be --N-- or --CR'--, in
which R' may be hydrogen or deuterium, and at least one of X.sup.5
to X.sup.7 may be --N--.
##STR00052##
[0067] In Chemical Formula 3, X.sup.1 to X.sup.4 may each
independently be --N--, --CR.sup.1--, --CR.sup.2--, --CR.sup.3-- or
--CR.sup.4--, R.sup.1 to R.sup.6 may each independently be a
hydrogen, deuterium, substituted or unsubstituted C1 to C20 alkyl
group, substituted or unsubstituted C6 to C30 aryl group,
substituted or unsubstituted C3 to C30 heteroaryl group, or a
combination thereof, L.sup.1 and L.sup.2 may each independently be
a single bond, substituted or unsubstituted C2 to C6 alkenyl group,
substituted or unsubstituted C2 to C6 alkynyl group, substituted or
unsubstituted C6 to C30 arylene group, substituted or unsubstituted
C3 to C30 heteroarylene group, or a combination thereof, n and m
may each independently be 1 or 2, Ar.sup.1 may be hydrogen,
deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a
substituted or unsubstituted C6 to C30 aryl group, a substituted or
unsubstituted C3 to C30 heteroaryl group, or a combination thereof,
X.sup.5 to X.sup.7 may each independently be --N-- or --CR'--,
wherein R' is hydrogen or deuterium, and at least one of X.sup.5 to
X.sup.7 may be --N--.
[0068] Compounds of the above Chemical Formulae 2 and 3 may have a
structure where, in the above Chemical Formula 1, one of Ar.sup.1
or Ar.sup.2 is a heteroaryl group including at least one nitrogen
atom.
[0069] The difference between structures of Chemical Formulae 2 and
3 may be the position of a substituent bound to the hetero fused
ring core.
[0070] When having the bonding position as in Chemical Formula 2,
thermal properties of the compound may be enforced by introducing
the rigid molecular structure.
[0071] When having the bonding position as in Chemical Formula 3,
amorphous characteristics of the compound may be enforced to
thereby help suppress the crystallinity, so the device using the
same may have a prolonged life span.
[0072] In an implementation, Ar.sup.2 (or Ar.sup.1) may be a
substituted or unsubstituted naphthyl group, a substituted or
unsubstituted anthracenyl group, a substituted or unsubstituted
phenanthrenyl group, a substituted or unsubstituted triphenylenyl
group, a substituted or unsubstituted pyrenyl group, a substituted
or unsubstituted chrysenyl group, or a combination thereof. When
having the substituent, the core may be more asymmetric to thereby
help decrease the crystallinity of the compound. Thus, when the
organic photoelectric device is fabricated using the compound
having low crystallinity, the life-span of device may be
improved.
[0073] In an implementation, the substituted or unsubstituted C3 to
C30 heteroaryl group having the electronic properties may be or may
include, e.g., a substituted or unsubstituted imidazolyl group, a
substituted or unsubstituted triazolyl group, a substituted or
unsubstituted tetrazolyl group, a substituted or unsubstituted
carbazolyl group, a substituted or unsubstituted oxadiazolyl group,
a substituted or unsubstituted oxatriazolyl group, a substituted or
unsubstituted thiatriazolyl group, a substituted or unsubstituted
benzimidazolyl group, a substituted or unsubstituted benzotriazolyl
group, a substituted or unsubstituted pyridinyl group, a
substituted or unsubstituted pyrimidinyl group, a substituted or
unsubstituted triazinyl group, a substituted or unsubstituted
pyrazinyl group, a substituted or unsubstituted pyridazinyl group,
a substituted or unsubstituted purinyl group, a substituted or
unsubstituted quinolinyl group, a substituted or unsubstituted
isoquinolinyl group, a substituted or unsubstituted phthalazinyl
group, a substituted or unsubstituted naphpyridinyl group, a
substituted or unsubstituted quinoxalinyl group, a substituted or
unsubstituted quinazolinyl group, a substituted or unsubstituted
acridinyl group, a substituted or unsubstituted phenanthrolinyl
group, a substituted or unsubstituted phenazinyl group, or a
combination thereof.
[0074] In an implementation, L.sup.1 and L.sup.2 may each
independently be, e.g., a substituted or unsubstituted ethenylene,
a substituted or unsubstituted ethynylene, a substituted or
unsubstituted phenylene, a substituted or unsubstituted
biphenylene, a substituted or unsubstituted naphthalene, a
substituted or unsubstituted pyridinylene, a substituted or
unsubstituted pyrimidinylene, a substituted or unsubstituted
triazinylene, substituted or unsubstituted quinolinylene,
substituted or unsubstituted quinoxalinylene, and the like.
[0075] As may be seen above, the substituent may have a .pi. bond.
Thus, the substituent may help increase a triplet energy band gap
by adjusting entire .pi.-conjugation length of the compound, so it
may be usefully applied for an emission layer of organic
photoelectric device as a phosphorescent host. In an
implementation, n and/or m may be 0, and the linking groups L.sup.1
and/or L.sup.2 may not be present in the compound.
[0076] In an implementation, the compound for an organic
optoelectronic device may be represented by one of the following
Chemical Formulae A1 to A63.
##STR00053## ##STR00054## ##STR00055## ##STR00056## ##STR00057##
##STR00058## ##STR00059## ##STR00060## ##STR00061## ##STR00062##
##STR00063## ##STR00064## ##STR00065## ##STR00066## ##STR00067##
##STR00068## ##STR00069## ##STR00070## ##STR00071## ##STR00072##
##STR00073##
[0077] In an implementation, the compound for an organic
optoelectronic device may be represented by one of the following
Chemical Formulae B1 to B72.
##STR00074## ##STR00075## ##STR00076## ##STR00077## ##STR00078##
##STR00079## ##STR00080## ##STR00081## ##STR00082## ##STR00083##
##STR00084## ##STR00085## ##STR00086## ##STR00087## ##STR00088##
##STR00089## ##STR00090## ##STR00091## ##STR00092## ##STR00093##
##STR00094## ##STR00095## ##STR00096## ##STR00097##
[0078] The compound for an organic optoelectronic device including
one of the above compounds may have a glass transition temperature
of greater than or equal to 110.degree. C., and a thermal
decomposition temperature of greater than or equal to 400.degree.
C., indicating improved thermal stability. Accordingly, it is
possible to produce an organic optoelectronic device having a high
efficiency.
[0079] The compound for an organic optoelectronic device including
one of the above compounds may play a role for emitting light or
injecting and/or transporting electrons, and may also act as a
light emitting host with an appropriate dopant. For example, the
compound for an organic optoelectronic device may be used as a
phosphorescent or fluorescent host material, a blue light emitting
dopant material, or an electron transport material.
[0080] The compound for an organic optoelectronic device according
to an embodiment may be used for an organic thin layer and may help
improve the life-span characteristic. Thus, efficiency
characteristic, electrochemical stability, and thermal stability of
an organic optoelectronic device may be improved, and the driving
voltage may be decreased.
[0081] Therefore, according to another embodiment, an organic
optoelectronic device that includes the compound for an organic
optoelectronic device may be provided. The organic optoelectronic
device may be, e.g., an organic photoelectric device, an organic
light emitting diode, an organic solar cell, an organic transistor,
an organic photo conductor drum, an organic memory device, or the
like. For example, the compound for an organic optoelectronic
device according to an embodiment may be included in an electrode
or an electrode buffer layer in the organic solar cell to help
improve the quantum efficiency, and/or it may be used as an
electrode material for a gate, a source-drain electrode, or the
like in the organic transistor.
[0082] Hereinafter, an organic light emitting diode is described in
detail.
[0083] According to another embodiment, an organic light emitting
diode may include an anode, a cathode, and at least one organic
thin layer between the anode and the cathode. The least one organic
thin layer may include the compound for an organic optoelectronic
device according to an embodiment.
[0084] The at least one organic thin layer may include a layer
selected from the group of an emission layer, a hole transport
layer (HTL), a hole injection layer (HIL), an electron transport
layer (ETL), an electron injection layer (EIL), a hole blocking
layer, and a combination thereof. The at least one organic thin
layer may include the compound for an organic optoelectronic device
according to an embodiment. For example, the compound for an
organic optoelectronic device according to an embodiment may be
included in an electron transport layer (ETL) or an electron
injection layer (EIL). In an implementation, when the compound for
an organic optoelectronic device is included in the emission layer,
the compound for an organic optoelectronic device may be included
as a phosphorescent or fluorescent host and/or as a fluorescent
blue dopant material.
[0085] FIGS. 1 to 5 illustrate cross-sectional views showing
organic light emitting diodes including the compound for an organic
optoelectronic device according to an embodiment.
[0086] Referring to FIGS. 1 to 5, organic light emitting diodes
100, 200, 300, 400, and 500 according to an embodiment may include
at least one organic thin layer 105 interposed between an anode 120
and a cathode 110.
[0087] The anode 120 may include an anode material having a large
work function to facilitate hole injection into an organic thin
layer. The anode material may include, e.g., a metal such as
nickel, platinum, vanadium, chromium, copper, zinc, and gold, or
alloys thereof; a metal oxide such as zinc oxide, indium oxide,
indium tin oxide (ITO), and indium zinc oxide (IZO); a combined
metal and oxide such as ZnO:Al or SnO.sub.2:Sb; or a conductive
polymer such as poly(3-methylthiophene),
poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDT), polypyrrole, and
polyaniline. In an implementation, a transparent electrode such as
indium tin oxide (ITO) may be included in an anode.
[0088] The cathode 110 may include a cathode material having a
small work function to facilitate electron injection into an
organic thin layer. The cathode material may include, e.g., a metal
such as magnesium, calcium, sodium, potassium, titanium, indium,
yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or
alloys thereof; or a multi-layered material such as LiF/Al, Liq/Al,
LiO.sub.2/Al, LiF/Ca, LiF/Al, and BaF.sub.2/Ca. In an
implementation, a metal electrode including aluminum may be
included in a cathode.
[0089] Referring to FIG. 1, the organic photoelectric device 100
may include an organic thin layer 105 including only an emission
layer 130.
[0090] Referring to FIG. 2, a double-layered organic photoelectric
device 200 may include an organic thin layer 105 including an
emission layer 230 including an electron transport layer (ETL), and
a hole transport layer (HTL) 140. As shown in FIG. 2, the organic
thin layer 105 may include a double layer of the emission layer 230
and hole transport layer (HTL) 140. The emission layer 230 may also
function as an electron transport layer (ETL), and the hole
transport layer (HTL) 140 layer may have an excellent binding
property with a transparent electrode such as ITO or an excellent
hole transport capability.
[0091] Referring to FIG. 3, a three-layered organic photoelectric
device 300 may include an organic thin layer 105 including an
electron transport layer (ETL) 150, an emission layer 130, and a
hole transport layer (HTL) 140. The emission layer 130 may be
independently installed, and layers having an excellent electron
transport capability or an excellent hole transport capability may
be separately stacked.
[0092] As shown in FIG. 4, a four-layered organic photoelectric
device 400 may include an organic thin layer 105 including an
electron injection layer (EIL) 160, an emission layer 130, a hole
transport layer (HTL) 140, and a hole injection layer (HIL) 170 for
adherence with the anode 120 of ITO.
[0093] As shown in FIG. 5, a five layered organic photoelectric
device 500 may include an organic thin layer 105 including an
electron transport layer (ETL) 150, an emission layer 130, a hole
transport layer (HTL) 140, and a hole injection layer (HIL) 170,
and further includes an electron injection layer (EIL) 160 to
achieve a low voltage.
[0094] In FIGS. 1 to 5, the organic thin layer 105 including at
least one selected from the group of an electron transport layer
(ETL) 150, an electron injection layer (EIL) 160, emission layers
130 and 230, a hole transport layer (HTL) 140, a hole injection
layer (HIL) 170, and combinations thereof may include the compound
for an organic optoelectronic device. The compound for an organic
optoelectronic device may be used for an electron transport layer
(ETL) 150 or electron injection layer (EIL) 160. When it is used
for the electron transport layer (ETL), it is possible to provide
an organic photoelectric device having a more simple structure
because an additional hole blocking layer (not shown) may be
omitted.
[0095] When the compound for an organic optoelectronic device is
included in the emission layers 130 and 230, the material for the
organic photoelectric device may be included as a phosphorescent or
fluorescent host or a fluorescent blue dopant.
[0096] The organic light emitting diode may be fabricated by, e.g.,
forming an anode on a substrate; forming an organic thin layer in
accordance with a dry coating method such as evaporation,
sputtering, plasma plating, and ion plating or a wet coating method
such as spin coating, dipping, and flow coating; and providing a
cathode thereon.
[0097] Another embodiment provides a display device including the
organic photoelectric device according to the above embodiment.
[0098] The following Examples and Comparative Examples are provided
in order to highlight characteristics of one or more embodiments,
but it will be understood that the Examples and Comparative
Examples are not to be construed as limiting the scope of the
embodiments, nor are the Comparative Examples to be construed as
being outside the scope of the embodiments. Further, it will be
understood that the embodiments are not limited to the particular
details described in the Examples and Comparative Examples.
[0099] (Preparation of Compound for Organic Photoelectric
Device)
EXAMPLE 1
Synthesis of Compound Represented by Chemical Formula A1
[0100] The compound represented by Chemical Formula A1 was
synthesized through 6 steps as shown in of the following Reaction
Scheme 1:
##STR00098## ##STR00099## ##STR00100##
[0101] First Step; Synthesis of Intermediate Product (A)
[0102] 27.3 g (160.1 mmol) of 2'-acetonaphtone, 25 g (160.1 mmol)
of 2-naphthaldehyde, and 9.6 g (240.2 mmol) of sodium hydroxide
were suspended in 700 mL of ethanol and agitated at room
temperature (.about.25.degree. C.) for 1 hour. The mixed solid was
extracted with chloroform and recrystallized with methanol to
provide 49 g (yield: 99%) of an intermediate product A.
[0103] Second Step; Synthesis of Intermediate Product (B)
[0104] 38 g (123.2 mmol) of the intermediate product (A), 34.8 g
(147.8 mmol) of 2-bromobenzidine hydrochloride, and 9.9 g (246.4
mmol) of sodium hydroxide were suspended in a mixed solvent of 380
mL of ethanol and 380 mL of tetrahydrofuran and heated and refluxed
at 80.degree. C. for 12 hours. After cooling, the deposited solid
was separated by a filter and rinsed with methanol to obtain 26.6 g
(yield: 44%) of an intermediate product (B).
[0105] Third Step: Synthesis of Intermediate Product (C)
[0106] 25 g (51.3 mmol) of the intermediate product (B), 15.6g
(61.6 mmol) of bis(pinacolato)diboron, 1.1 g (1.3 mmol) of
[1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II), and
15.1 g (153.9 mmol) of potassium acetate were suspended in 600 mL
of toluene and agitated at 120.degree. C. for 12 hours. After
cooling, the reaction solution was poured in distilled water to
deposit a solid, and it was filtered and separated. The filtered
solid was recrystallized with ethyl acetate/hexane to provide 18.4
g (yield: 67%) of the intermediate product (C).
[0107] Fourth Step; Synthesis of Intermediate Product (D)
[0108] 31.6 g (126.9 mmol) of 2-bromoacetylnaphthalene and 14.3 g
(152.2 mmol) of 2-aminopyridine were suspended in 300 mL of ethanol
and agitated at 80.degree. C. for 12 hours. After cooling, ethanol
was distilled and residues were separated by a filter, and rinsed
with a sodium hydrogen carbonate aqueous solution. The solid was
recrystallized with a methanol/water mixed solvent to obtain 32.7 g
(yield: 99%) of an intermediate product (D).
[0109] Fifth Step; Synthesis of Intermediate Product (E)
[0110] 31 g (127 mmol) of the intermediate product (D) and 31.4 g
(140 mmol) of N-iodosuccinimide (NIS) were suspended in 600 mL of
acetonitrile and agitated at 50.degree. C. for 1 hour. After
cooling, the mixture was poured into 800 mL of water followed by
extraction with methylene chloride and distillation under a reduced
pressure. The residues were recrystallized with methanol to provide
17.5 g (yield: 37%) of an intermediate product (E).
[0111] Sixth Step: Synthesis of Compound of Chemical Formula A1
[0112] 4.3 g (11.6 mmol) of the intermediate product (E), 7.4 g
(13.9 mmol) of the intermediate product (C), 0.34 g (0.29 mmol) of
tetrakis(triphenylphosphine)palladium, and 3.2 g (23.2 mmol) of
potassium carbonate were suspended in a mixed solvent of 160 mL of
tetrahydrofuran and 80 mL of water, and suspended and agitated at
80.degree. C. for 12 hours. After cooling, the reaction fluid was
separated into two layers, and then an organic layer was cleaned
with a saturated sodium chloride aqueous solution and dried with
anhydrous sodium sulfate. The organic solvent was removed by
distillation under a reduced pressure, and the residues were
recrystallized with methanol and ethyl acetate to provide 4.94 g
(yield: 65%) of a compound. (element analysis/Calcd: C, 86.74; H,
4.65; N, 8.61, Found, C, 86.77; H, 4.63; N, 8.60)
EXAMPLE 2
Synthesis of Compound Represented by Chemical Formula B6
[0113] The compound represented by Chemical Formula B6 was
synthesized through 3 steps as shown in the following Reaction
Scheme 2:
##STR00101## ##STR00102##
[0114] First Step; Synthesis of Intermediate Product (F)
[0115] 50 g (180 mmol) of 4-bromophenacyl bromide and 20.3 g (220
mmol) of 2-aminopyridine were suspended in 300 mL of ethanol and
agitated at 80.degree. C. for 12 hours. After cooling, ethanol was
distilled and residues were separated by filter, and then resultant
was rinsed with a sodium hydrogen carbonate aqueous solution. The
solid was recrystallized with a methanol/water mixed solvent to
provide 32.7 g (yield: 99%) of an intermediate product (F).
[0116] Second Step; Synthesis of Intermediate Product (G)
[0117] 17 g (62.2 mmol) of the intermediate product (F), 19 g (74.6
mmol) of bis(pinacolato)diboron, 1.5 g (1.6 mmol) of
[1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II), and
18.3 g (186.6 mmol) of potassium acetate were suspended in 180 mL
of dimethylformaldehyde and agitated at 80.degree. C. for 12 hours.
After cooling, the reaction solution was poured in distilled water
to deposit a solid, and it was filtered and separated. The filtered
solid was recrystallized with ethyl acetate/hexane to provide 8.9 g
(yield: 44%) of the intermediate product (C).
[0118] Third Step: Synthesis of Compound of Chemical Formula B2
[0119] 10.7 g (23 mmol) of
2-chloro-4-(phenanthren-10-yl)-6-(phenanthren-9-yl)pyrimidine, 8.8
g (27.6 mmol) of the intermediate product (G), 0.66 g (0.58 mmol)
of tetrakis(triphenylphosphine)palladium, and 9.5 g (69 mmol) of
potassium carbonate were suspended in a mixed solvent of 200 mL of
tetrahydrofuran and 100 mL of water and agitated at 80.degree. C.
for 12 hours. After cooling, the reaction fluid was separated into
two layers, and then an organic layer was cleaned with a saturated
sodium chloride aqueous solution and dried with anhydrous sodium
sulfate. The organic solvent was removed by distillation under a
reduced pressure, and the residues were recrystallized with
methanol and ethyl acetate to provide 9.8 g (yield: 68%) of a
compound. (element analysis/Calcd: C, 86.51; H, 4.52; N, 8.97,
Found, C, 86.56; H, 4.49; N, 8.94)
[0120] (Manufacture of Organic Light Emitting Diode)
EXAMPLE 3
[0121] An organic photoelectric device was fabricated using a 1,000
.ANG.-thick ITO layer as an anode and a 1,000 .ANG.-thick aluminum
(Al) layer as a cathode.
[0122] In particular, the anode was prepared cutting an ITO glass
substrate having a sheet resistance of 15 .OMEGA./cm.sup.2 into a
size of 50 mm.times.50 mm.times.0.7 mm and cleaning it in acetone,
isopropyl alcohol, and pure water, respectively for 5 minutes and
with UV ozone for 30 minutes.
[0123] Then,
N1,N1'-(biphenyl-4,4'-diyl)bis(N1-(naphthalen-2-yl)-N4,N4-diphenylbenzene-
-1,4-diamine) was deposited to be 65 nm thick as a hole injection
layer (HIL) on the glass substrate, and
N,N'-di(1-naphthyl)-N,N'-diphenylbenzidine was deposited to be 40
nm thick as a hole transport layer (HTL).
[0124] Then, 4% of
N,N,N',N'-tetrakis(3,4-dimethylphenyl)chrysene-6,12-diamine and 96%
of 9-(3-(naphthalen-1-yl)phenyl)-10-(naphthalen-2-yl)anthracene
were deposited to be 25 nm thick as an emission layer on the hole
transport layer (HTL).
[0125] Then, the compound according to Example 1 was deposited to
be 30 nm thick on the emission layer as an electron transport layer
(ETL).
[0126] On the electron transport layer (ETL), Liq was
vacuum-deposited to be 0.5 nm thick on the electron injection layer
(EIL), and Al was vacuum-deposited to be 100 nm thick, forming a
Liq/Al electrode.
EXAMPLE 4
[0127] An organic light emitting diode was fabricated in accordance
with the same procedure as in Example 3, except that the electron
transport layer (ETL) was fabricated by using the compound obtained
in Example 2 instead of the compound obtained in Example 1.
EXAMPLE 5
[0128] An organic light emitting diode was fabricated in accordance
with the same procedure as in Example 3, except that the electron
transport layer (ETL) was fabricated by depositing the compound
obtained in Example 1 and Liq at 1:1 (v/v) instead of the compound
obtained in Example 1.
EXAMPLE 6
[0129] An organic light emitting diode was fabricated in accordance
with the same procedure as in Example 3, except that the electron
transport layer (ETL) was fabricated by depositing the compound
obtained in Example 2 and Liq at 1:1 (v/v) instead of the compound
obtained in Example 1.
COMPARATIVE EXAMPLE 1
[0130] An organic light emitting diode was fabricated in accordance
with the same procedure as in Example 3, except that the electron
transport layer (ETL) was fabricated by using the compound of the
following Chemical Formula ET1 instead of the compound obtained of
Chemical Formula A1 in Example 1.
##STR00103##
COMPARATIVE EXAMPLE 2
[0131] An organic light emitting diode was fabricated in accordance
with the same procedure as in Example 5, except that the electron
transport layer (ETL) was fabricated by using the compound of the
above Chemical Formula ET1 (with Liq) instead of the compound
obtained of Chemical Formula A1 in Example 1.
[0132] (Performance Measurement of Organic Light Emitting
Diode)
EXPERIMENTAL EXAMPLE
[0133] Each of the obtained organic photoelectric devices according
to Examples 3, 4, 5, 6, and Comparative Examples 1 and 2 was
measured for luminance change, current density change depending
upon the voltage, and luminous efficiency. The specific method was
as follows. The results are shown in the following Table 1 and in
FIGS. 6 to 13.
[0134] (1) Measurement of Current Density Change Depending on
Voltage Change
[0135] The obtained organic light emitting diode was measured for
current value flowing in the unit device while increasing the
voltage from 0 V to 10 V using a current-voltage meter (Keithley
2400), and the measured current value was divided by area to
provide the result.
[0136] (2) Measurement of Luminance Change Depending on Voltage
Change
[0137] The organic light emitting diode was measured for luminance
using a luminance meter (Minolta Cs-1000A) while increasing the
voltage from 0 V to 10 V.
[0138] (3) Measurement of Luminous Efficiency
[0139] Current efficiency (cd/A) and electric power efficiency
(lm/W) at the same luminance (1,000 cd/m.sup.2) were calculated by
using luminance and current density from (1) and (2) and
voltage.
[0140] FIG. 6 illustrates a graph showing changes in current
density depending on a voltage of devices according to Examples 3
and 4, and Comparative Example 1.
[0141] FIG. 7 illustrates a graph showing changes in current
density depending on a voltage of devices according to Examples 5
and 6, and Comparative Example 2.
[0142] FIG. 8 illustrates a graph showing changes in luminance
depending on a voltage of devices according to Examples 3 and 4,
and Comparative Example 1.
[0143] FIG. 9 illustrates a graph showing changes in luminance
depending on a voltage of devices according to Examples 5 and 6,
and Comparative Example 2.
[0144] FIG. 10 illustrates a graph showing changes in luminous
efficiency depending on luminance of devices according to Examples
3 and 4, and Comparative Example 1.
[0145] FIG. 11 illustrates a graph showing changes in luminous
efficiency depending on luminance of devices according to Examples
5 and 6, and Comparative Example 2.
[0146] FIG. 12 illustrates a graph showing changes in electric
power efficiency depending on luminance of devices according to
Examples 3 and 4, and Comparative Example 1.
[0147] FIG. 13 illustrates a graph showing changes in electric
power efficiency depending on luminance of devices according to
Examples 5 and 6, and Comparative Example 2.
TABLE-US-00001 TABLE 1 Luminance 500 cd/m.sup.2 Luminous Electric
power Driving voltage efficiency efficiency CIE (V) (cd/A) (lm/W) x
y Example 3 4.4 5.0 3.6 0.14 0.05 Example 4 4.2 5.6 4.2 0.14 0.05
Comparative 5.2 3.3 2.0 0.14 0.05 Example 1 Example 5 3.8 6.6 5.4
0.14 0.04 Example 6 4.2 5.7 4.3 0.14 0.05 Comparative 4.4 5.4 3.9
0.14 0.06 Example 2
[0148] As may be seen in Table 1, the organic light emitting diodes
according to Examples 3 and 4 exhibited excellent luminous
efficiency and electric power efficiency with a low driving
voltage, compared to that of Comparative Example 1.
[0149] It may also be seen that the organic light emitting diode
according to Examples 5 and 6 exhibited excellent luminous
efficiency and electric power efficiency with a low driving
voltage, compared to that of Comparative Example 2.
[0150] By way of summation and review, an organic light emitting
diode (OLED) has recently drawn attention due to an increasing
demand for a flat panel display. In general, organic light emission
refers to conversion of electrical energy into photo-energy.
[0151] Such an organic light emitting diode may convert electrical
energy into light by applying current to an organic light emitting
material. It may have a structure in which a functional organic
material layer is interposed between an anode and a cathode. The
organic material layer may include a multi-layer including
different materials, e.g., a hole injection layer (HIL), a hole
transport layer (HTL), an emission layer, an electron transport
layer (ETL), and an electron injection layer (EIL), in order to
help improve efficiency and stability of an organic photoelectric
device.
[0152] In such an organic light emitting diode, when a voltage is
applied between an anode and a cathode, holes from the anode and
electrons from the cathode may be injected to the organic material
layer and recombined to generate excitons having high energy. The
generated excitons may generate light having certain wavelengths
while shifting to a ground state.
[0153] A phosphorescent light emitting material may be used for a
light emitting material of an organic light emitting diode, in
addition to the fluorescent light emitting material. Such a
phosphorescent material may emit light by transporting the
electrons from a ground state to an exited state, non-radiance
transiting of a singlet exciton to a triplet exciton through
intersystem crossing, and transiting a triplet exciton to a ground
state to emit light.
[0154] As described above, in an organic light emitting diode, an
organic material layer may include a light emitting material and a
charge transport material, e.g., a hole injection material, a hole
transport material, an electron transport material, an electron
injection material, and the like.
[0155] The light emitting material may be classified as blue,
green, and red light emitting materials according to emitted
colors, and yellow and orange light emitting materials to emit
colors approaching natural colors.
[0156] When one material is used as a light emitting material, a
maximum light emitting wavelength may be shifted to a long
wavelength or color purity may decrease because of interactions
between molecules, or device efficiency may decrease because of a
light emitting quenching effect. Therefore, a host/dopant system
may be included as a light emitting material in order to help
improve color purity and to help increase luminous efficiency and
stability through energy transfer.
[0157] In order to implement excellent performance of an organic
light emitting diode, a material constituting an organic material
layer, e.g., a hole injection material, a hole transport material,
a light emitting material, an electron transport material, an
electron injection material, and/or a light emitting material such
as a host and/or a dopant, should be stable and have good
efficiency. In addition, the material may be useful for other
organic photoelectric devices.
[0158] A low molecular weight organic light emitting diode may be
manufactured as a thin film in a vacuum deposition method and may
have good efficiency and life-span performance. A polymer organic
light emitting diode may be manufactured using an Inkjet or spin
coating method, and may have an advantage of low initial cost and
being large-sized.
[0159] Both low molecular weight organic light emitting and polymer
organic light emitting diodes may have an advantage of being
self-light emitting, having high speed response, wide viewing
angle, ultra-thin, high image quality, durability, large driving
temperature range, and the like. For example, they may have good
visibility due to self-light emitting characteristics, compared
with a LCD (liquid crystal display), and may have an advantage of
decreasing thickness and weight of LCD up to a third, because a
backlight is not required.
[0160] In addition, since they may have a response speed of a
microsecond unit, which is 1,000 time faster than an LCD, they may
realize a perfect motion picture without after-image. Based on
these advantages, they have been remarkably developed to have 80
times efficiency and more than 100 times life-span since their
initial introduction. Recently, they keep being rapidly larger such
as a 40-inch organic light emitting diode panel.
[0161] Simultaneously exhibiting improved luminous efficiency and
life-span in order to be larger may be particularly desirable. For
example, luminous efficiency may require smooth combination between
holes and electrons in an emission layer. However, an organic
material in general may have slower electron mobility than hole
mobility. Thus, it may exhibit an inefficient combination between
holes and electrons. Accordingly, it may be desirable to increase
electron injection and mobility from a cathode while simultaneously
preventing movement of holes.
[0162] In order to improve life-span, a material crystallization
caused by Joule heating generated during device operating should be
prevented. Accordingly, the embodiments provide an organic compound
having excellent electron injection and mobility, and high
electrochemical stability.
[0163] The embodiments provide a compound for an organic
optoelectronic device that may act as light emitting, or electron
injection and/or transport material, and also act as a light
emitting host along with an appropriate dopant is provided.
[0164] The embodiments provide an organic optoelectronic device
having excellent life-span, efficiency, driving voltage,
electrochemical stability, and thermal stability.
[0165] An organic optoelectronic device having excellent
electrochemical and thermal stability and life-span
characteristics, and high luminous efficiency at a low driving
voltage may be provided.
[0166] Example embodiments have been disclosed herein, and although
specific terms are employed, they are used and are to be
interpreted in a generic and descriptive sense only and not for
purpose of limitation. In some instances, as would be apparent to
one of ordinary skill in the art as of the filing of the present
application, features, characteristics, and/or elements described
in connection with a particular embodiment may be used singly or in
combination with features, characteristics, and/or elements
described in connection with other embodiments unless otherwise
specifically indicated. Accordingly, it will be understood by those
of skill in the art that various changes in form and details may be
made without departing from the spirit and scope of the present
invention as set forth in the following claims.
* * * * *